The present invention relates to a process for preparing 5-acyl-2-(furfurylthio)dihydro-2,5-dialkyl-3-[2H]furanones. Compositions using one or more of such 5-acyl-2-(furfurylthio)dihydro-2,5-dialkyl-3-[2H]furanones or "cis" or "trans" isomers thereof alter, modify, augment or enhance the flavor and/or aroma of consumable materials or impart flavor and/or aroma to consumable materials.
There has been considerable work performed relating to substances which can be used to impart (modify, augment or enhance) flavors to (or in) various consumable materials. These substances are used to diminish the use of natural products, some of which may be in short supply and to provide more uniform properties in the finished product. Coffee-like, roasted, cocoa-like, caramel-like, licorice, and roasted almond aroma and flavor characteristics are particularly desirable for many uses in foodstuff flavors, chewing gum flavors, toothpaste flavors and medicinal product flavors. Sweet, caramel/coffee aromas and flavors prior to smoking and sweet, caramel/coffee, nutty/pyrazine and roasted nutty aroma and taste characteristics on smoking are particularly desirable in tobaccos as well as tobacco flavoring compositions and in tobacco substitutes and flavoring compositions for such tobacco substitutes.
When one mole of diactyl is reacted with one mole of furfuryl mercaptan a coffee flavored reaction product is produced which has been found to contain a small percentage (about 10% by weight) of 5-actyl-2-(furfurylthio)dihydro-2,5-dimethyl-3-[2H]furanone with one of the "cis" - "trans" isomers in a ratio to the other of the "cis" - "trans" isomers being about 2:1. The process for preparing such a reaction product (without describing the constituents of the products) is set forth in Swiss Pat. No. 128,720 published on Nov. 16, 1928. It is stated in the example at column 2 on page 1 thereof that when one mixes furfuryl-2-mercaptan and diacetyl the product (alpha-oxy-alpha-acetylethyl)furfuryl-2-sulfide is produced. There is no disclosure in Swiss Pat. No. 128,720 that an additional mole of diacetyl added to the resulting reaction product will produce the compound having the structure: ##STR1## or any of its "cis" or "trans" isomers having the structures: ##STR2## In addition there is no disclosure either explicit or implicit in Swiss Pat. No. 128,720 that the compound having the structure: ##STR3## can be produced having a very high intensity and long lasting aroma and taste characteristics of the nature described herein.
U.S. Pat. No. 1,696,419 issued on Dec. 25, 1928 (Title: "Method of Producing Artificial Coffee Aroma") discloses the production of a coffee flavor using:
"one part of diacetyl, four parts of acetyl propionyl, four parts of methyl ethyl acetaldehyde, three parts of acetaldehyde, two parts of alpha methyl furfural, one part of furfural, three parts of pyridine, two parts of isovaleric acid, one part of phenol, one part of isoeugenol, 0.5 parts of guiacol, 0.5 parts of alpha methyl cyclopentenolone, 0.6 parts of methyl mercaptan, 0.3 parts of furfuryl mercaptan, 0.3 parts of n-octyl alcohol and 0.4 parts of thioguiacol"
at page 3, column 1, lines 29-39.
The compound having the structure: ##STR4## is not indicated to be produced as a result of admixing at higher temperatures the foregoing ingredients.
Nothing in the prior art discloses the reaction of a dimer of an alpha beta diketone having from 4 up to 6 carbon atoms with furfuryl mercaptan to form the genus of compounds having the structure: ##STR5##
Canadian Pat. No. 1,002,383 entitled: "Popcorn-Like Flavor and Process for Preparing Same" issued on Dec. 28, 1976 discloses the use of the reaction product of glyoxal or glycol aldehyde with a sulfur containing compound such as hydrogen sulfide to form a popcorn flavorant. Other sulfur containing compounds listed are L-Cysteine and other dicarbonyl compounds set forth in 1,002,383 are 2,3-pentanedione and 2,4-pentanedione but is indicated on page 8 of Canadian Pat. No. 1,002,383 that these other dicarbonyl compounds do not give the same effect as glyoxal or glycol aldehyde. None of the reaction products disclosed teach either explicitly or implicitly the process of our invention.